Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene
Tetrahydropyrene and pyrene have been functionalized in their 2,7-positions with carbazole and 3,6-di-tert-butylcarbazole groups, and the properties of these new compounds are compared to analogous carbazole and 3,6-di-tert-butylcarbazole derivatives of benzene and biphenyl using X-ray crystallograp...
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| Other Authors: | , , , , , , , , , |
| Format: | article |
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2013
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| Online Access: | http://hdl.handle.net/10725/6491 http://dx.doi.org/10.1039/C2TC00474G http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php http://pubs.rsc.org/-/content/articlehtml/2013/tc/c2tc00474g |
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| Summary: | Tetrahydropyrene and pyrene have been functionalized in their 2,7-positions with carbazole and 3,6-di-tert-butylcarbazole groups, and the properties of these new compounds are compared to analogous carbazole and 3,6-di-tert-butylcarbazole derivatives of benzene and biphenyl using X-ray crystallography, UV-vis absorption and fluorescence spectroscopy, electrochemistry, and quantum-chemical calculations. The absorption spectra are similar to those of their biphenyl-bridged analogues, although TD-DFT calculations indicate a different description of the excited states in the pyrene case, with the lowest observed absorption no longer corresponding to the S0 → S1 transition. The 3,6-di-tert-butylcarbazole compounds show reversible electrochemical oxidations; the benzene, biphenyl, tetrahydropyrene, or pyrene bridging groups have little impact on the first oxidation potential. Bilayer organic light-emitting diodes incorporating the tetrahydropyrene and pyrene derivatives as emitters show deep-blue electroluminescence. |
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